B(C<sub>6</sub>F<sub>5</sub>)<sub>3</sub>-Catalyzed Diastereoselective and Divergent Reactions of Vinyldiazo Esters with Nitrones: Synthesis of Highly Functionalized Diazo Compounds
Katarína Stefkova, Michael G. Guerzoni, Yara van Ingen, Emma Richards, Rebecca L. Melen
Abstract
High Resolution Image Download MS PowerPoint Slide Herein we report a mild, transition-metal-free, highly diastereoselective Lewis acid catalyzed methodology toward the synthesis of isoxazolidine-based diazo compounds from the reaction between vinyldiazo esters and nitrones. Interestingly, the isoxazolidine products were identified to have contrasting diastereoselectivity to previously reported metal-catalyzed reactions. Furthermore, the same catalyst can be used with enol diazo esters, prompting the formation of Mukaiyama–Mannich products. These diazo products can then be further functionalized to afford benzo[ b ]azepine and pyrrolidinone derivatives.
Topics & Concepts
DiazoChemistryCatalysisEnolOrganic chemistryLewis acids and basesMannich reactionTransition metalCombinatorial chemistryCyclopropane Reaction MechanismsCatalytic C–H Functionalization MethodsCatalytic Cross-Coupling Reactions